Showing metabocard for Oxoadipic acid (MMDBc0029483)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:24:07 UTC
Update Date2024-04-30 19:35:56 UTC
Metabolite IDMMDBc0029483
Metabolite Identification
Common NameOxoadipic acid
Description2-Oxoadipic acid is produced from lysine in the cytosol of cells via the saccharopine and the pipecolic acid pathways. Catabolites of hydroxylysine and tryptophan enter these pathways as 2-aminoadipic- -semialdehyde and 2-oxoadipate, respectively. In the cytoplasm, 2-oxoadipate is decarboxylated to glutaryl-CoA by the 2-oxoadipate dehydrogenase complex and then converted to acetyl-CoA.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fdb71cd3cd8>

Oxoadipic acid.mol
  Mrv1652309032023582D          

 11 10  0  0  0  0            999 V2000
   -1.7862    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  7  2  0  0  0  0
  1  8  1  0  0  0  0
  6  9  2  0  0  0  0
  6 10  1  0  0  0  0
  2 11  2  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007fdb71cd3cd8>

HMDB0000225
     RDKit          3D
Oxoadipic acid
 19 18  0  0  0  0  0  0  0  0999 V2000
    1.6355   -1.5653    0.7580 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3373   -0.7801    0.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7175   -0.7887    0.3479 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8379    0.1622   -0.9098 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3498    0.0980   -0.9932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3601    0.4780    0.2611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8288    0.3805    0.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2566    0.0161   -1.0517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7888    0.6891    1.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3683    1.0588    2.2509 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1586    0.5976    0.9255 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0285   -0.5239    1.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2141    1.1828   -0.6551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2714   -0.0604   -1.9110 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0062    0.7644   -1.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0935   -0.9555   -1.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1713    1.5833    0.4175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0496   -0.1067    1.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5096    0.4050   -0.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
  5 16  1  0
  6 17  1  0
  6 18  1  0
 11 19  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007fdb71cd3cd8>

Oxoadipic acid.mol
  Mrv1652309032023582D          

 11 10  0  0  0  0            999 V2000
   -1.7862    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  7  2  0  0  0  0
  1  8  1  0  0  0  0
  6  9  2  0  0  0  0
  6 10  1  0  0  0  0
  2 11  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029483

> <DATABASE_NAME>
MIME

> <SMILES>
OC(=O)CCCC(=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H8O5/c7-4(6(10)11)2-1-3-5(8)9/h1-3H2,(H,8,9)(H,10,11)

> <INCHI_KEY>
FGSBNBBHOZHUBO-UHFFFAOYSA-N

> <FORMULA>
C6H8O5

> <MOLECULAR_WEIGHT>
160.1247

> <EXACT_MASS>
160.037173366

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
14.159721281418744

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-oxohexanedioic acid

> <ALOGPS_LOGP>
-0.37

> <JCHEM_LOGP>
0.33530536533333316

> <ALOGPS_LOGS>
-0.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.035296902862189

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.842680623658864

> <JCHEM_PKA_STRONGEST_BASIC>
-9.657072598097674

> <JCHEM_POLAR_SURFACE_AREA>
91.66999999999999

> <JCHEM_REFRACTIVITY>
33.484

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.34e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
oxoadipate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007fdb71cd3cd8>

HMDB0000225
     RDKit          3D
Oxoadipic acid
 19 18  0  0  0  0  0  0  0  0999 V2000
    1.6355   -1.5653    0.7580 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3373   -0.7801    0.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7175   -0.7887    0.3479 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8379    0.1622   -0.9098 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3498    0.0980   -0.9932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3601    0.4780    0.2611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8288    0.3805    0.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2566    0.0161   -1.0517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7888    0.6891    1.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3683    1.0588    2.2509 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1586    0.5976    0.9255 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0285   -0.5239    1.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2141    1.1828   -0.6551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2714   -0.0604   -1.9110 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0062    0.7644   -1.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0935   -0.9555   -1.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1713    1.5833    0.4175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0496   -0.1067    1.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5096    0.4050   -0.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
  5 16  1  0
  6 17  1  0
  6 18  1  0
 11 19  1  0
M  END
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PDB for #<Metabolite:0x00007fdb71cd3cd8>

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Oxoadipic acid.mol                                
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  C   UNK     0      -3.334   0.385   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.001  -0.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.667   0.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.667  -0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.001   0.385   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.334  -0.385   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.334   1.925   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -4.668  -0.385   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       3.334  -1.925   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       4.668   0.385   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -2.001  -1.925   0.000  0.00  0.00           O+0
CONECT    1    2    7    8                                                  
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    9   10                                                  
CONECT    7    1                                                            
CONECT    8    1                                                            
CONECT    9    6                                                            
CONECT   10    6                                                            
CONECT   11    2                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END
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3D PDB for #<Metabolite:0x00007fdb71cd3cd8>

COMPND    HMDB0000225
HETATM    1  O1  UNL     1       1.635  -1.565   0.758  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.337  -0.780   0.104  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.717  -0.789   0.348  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.838   0.162  -0.910  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.350   0.098  -0.993  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.360   0.478   0.261  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.829   0.380   0.066  1.00  0.00           C  
HETATM    8  O3  UNL     1      -2.257   0.016  -1.052  1.00  0.00           O  
HETATM    9  C6  UNL     1      -2.789   0.689   1.113  1.00  0.00           C  
HETATM   10  O4  UNL     1      -2.368   1.059   2.251  1.00  0.00           O  
HETATM   11  O5  UNL     1      -4.159   0.598   0.925  1.00  0.00           O  
HETATM   12  H1  UNL     1       4.029  -0.524   1.273  1.00  0.00           H  
HETATM   13  H2  UNL     1       2.214   1.183  -0.655  1.00  0.00           H  
HETATM   14  H3  UNL     1       2.271  -0.060  -1.911  1.00  0.00           H  
HETATM   15  H4  UNL     1       0.006   0.764  -1.831  1.00  0.00           H  
HETATM   16  H5  UNL     1       0.094  -0.956  -1.282  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.171   1.583   0.418  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.050  -0.107   1.128  1.00  0.00           H  
HETATM   19  H8  UNL     1      -4.510   0.405  -0.010  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   12
CONECT    4    5   13   14
CONECT    5    6   15   16
CONECT    6    7   17   18
CONECT    7    8    8    9
CONECT    9   10   10   11
CONECT   11   19
END
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SMILES for #<Metabolite:0x00007fdb71cd3cd8>

OC(=O)CCCC(=O)C(O)=O
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INCHI for #<Metabolite:0x00007fdb71cd3cd8>

InChI=1S/C6H8O5/c7-4(6(10)11)2-1-3-5(8)9/h1-3H2,(H,8,9)(H,10,11)
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Synonyms
ValueSource
2-OxoadipateChEBI
2-Oxoadipic acidKegg
OxoadipateGenerator
2-Keto-adipateHMDB
2-KetoadipateHMDB
2-Ketoadipic acidHMDB
2-oxo-HexanedioateHMDB
2-oxo-Hexanedioic acidHMDB
2-OxohexanedioateHMDB
2-Oxohexanedioic acidHMDB
2-Oxohexanedionic acidHMDB
a-KetoadipateHMDB
a-Ketoadipic acidHMDB
a-OxoadipateHMDB
a-Oxoadipic acidHMDB
alpha-KetoadipateHMDB
alpha-Ketoadipic acidHMDB
alpha-OxoadipateHMDB
alpha-Oxoadipic acidHMDB
α-Ketoadipic acidHMDB
α-Oxoadipic acidHMDB
Molecular FormulaC6H8O5
Average Mass160.1247
Monoisotopic Mass160.037173366
IUPAC Name2-oxohexanedioic acid
Traditional Nameoxoadipate
CAS Registry Number3184-35-8
SMILES
OC(=O)CCCC(=O)C(O)=O
InChI Identifier
InChI=1S/C6H8O5/c7-4(6(10)11)2-1-3-5(8)9/h1-3H2,(H,8,9)(H,10,11)
InChI KeyFGSBNBBHOZHUBO-UHFFFAOYSA-N